Addition of diazocyclopropane generated in situ to acrylic acid derivatives and transformations of resulting functionally substituted spiro(pyrazolinecyclopropanes)

Article abstract of DOI:10.1007/BF02495406

The reaction of diazocyclopropane generated in situ with acrylonitrile or methyl acrylate to give 1 : 1, 1 : 2, and 2 : 1 cycloadducts was carried out. The products resulting from 1.3-dipolar cycloaddition and subsequent isomerization, viz., 3-cyano- and 3-methoxycarbonylspiro(2-pyrazoline-5,1 ′-cyclopropanes), isolated in the first step in -70% yield, react in an alkaline solution with the above acrylates or diazocyclopropane as C(3)-nucleophiles to give the corresponding 3-(2′-cyanoethyl)-, 3-(2′-methoxycarbonylethyl)-, or 3-(cyclopropylazo)-1-pyrazolines. The thermal deazotization of these pyrazolines to spiropentane derivatives was investigated.